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The Self-Made Man: Jack Dorsey

Entrepreneurs come in many shapes and sizes, and work in many different industries, but most of them spend their careers building and refining one basic idea. It’s rare that an entrepreneur successfully breaks ground with two separate concepts, yet this week’s Self Made Man—Twitter and Square creator Jack Dorsey—did just that.

Jack was born and raised in St. Louis, and was that adorable kind of Catholic nerd who got way into a really weird hobby. In his case, it was dispatch routing. I mean, what 13-year-old decides that’s their thing? Aside from Jack, I can’t think of any.

As a side note, a lot of taxi cab companies still use the dispatch logistics software he created back in the day.

Anyway, Jack came up with Twitter when, after being inspired by the success of Livejournal and AOL Instant Messenger, he experimented with the idea of a Web-based short message communication service that could be updated in real-time.

It’s hard to imagine, but yes, there was a time when Livejournal was good for more than furry porn and getting hacked by Russians every six months.

Jack put together a prototype of Twitter two weeks after his initial idea, and tried to make it as easy to share with friends as possible, which attracted enough venture capital investment to get it off the ground. It’s been growing like a weed ever since.

Square, which was Jack’s second big idea, was inspired by the age-old problem of an individual seller (in this case, a friend of Jack’s who was trying to unload $2,000 worth of glass faucets and fittings) not being able to accept credit cards. Jack wondered if there was a way to read credit cards on a smartphone, since they can already do anything else, and he developed the Square reader (which he almost named Squirrel, Stash, and Wallet before deciding on the current name) based on that.

In both cases, Jack came up with disruptive ideas that were simple enough to implement quickly and clever enough to attract start-up capital. He’s always thinking, which is something that any budding entrepreneurs reading this right now should keep in mind.

Also, don’t let any of your weird, goofy hobbies fall by the wayside. You never know which one will make you richer than God, albeit in a totally roundabout, impossible-to-predict way.

I’ll leave you with this video Jack Dorsey talking about his career and offering advice to students at the Stanford Graduate School of Business. It’s a long one, clocking in at 44 minutes or so, but it’s time well spent, I assure you.

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About Dave Kiefaber Dave Kiefaber is a Baltimore-based writer who regularly contributes to Adfreak and the Gettysburg Times. His personal website is at

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